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The Night I Was Shaq’s Wingman

February 6, 2007
Boston, Massachusetts

As an autograph collector I’m used to asking celebrities. Asking them to sign something. Asking them to take a picture with me. But never before has a famous person asked me for something. That is, until Shaq asked me to be his wingman.

I had been sitting on the lobby sofa of the Four Seasons for over a half hour and still hadn’t seen any tall black guys. And I was beginning to lose my patience.

Shaq and Matt Raymond

Picture taken moments before Shaq enlisted Matt’s help picking up a young woman.

The hotel’s revolving door spun perpetually as the after-work crowd trickled in for drinks and early dinners. Outside, a never-ending stream of black sedans and SUVs swapped drivers and disappeared. A middle-aged woman with twenty-year old legs clicked by on the arm of money. Everything about this place was gorgeous … and gross.

My buddies Garett and Lewando sat beside me, our eyes locked on a full-length mirror which offered a view of the elevator doors hidden around the corner. When I noticed the shadow appear in the reflection, I stopped breathing. Like when you’re at a school dance and your crush is suddenly twenty feet in front of you without a partner. You’ve got one shot but the fear of rejection is a pair of cement shoes.

Shaquille O’Neal strutted toward us in a long chocolate mink coat—a garment that perhaps single-handedly moved the animal a step closer to the endangered species list. With a blue and red knit skull cap pulled tightly over his massive round head, Shaq moved in slow motion. When he was within range, we engaged cautiously but confidently like you would a girl at a bar—carrying yourself without reservation, but giving yourself time to read and react to body language. Fortunately, Shaq had a rep for being a good signer, uncommon for a superstar of his ilk. Garett reached him first with a mini ball and slipped me his digital camera. I tucked my own ball between my elbow and ribs and took a step back to get both smiling faces in the viewfinder before snapping the memory.

“Dude, can you take a picture of me and Shaq?” Lewando asked.

I grew even more anxious, knowing every additional request increased the risk I would get shutout. After taking the picture I finally approached Shaq…only to see him heading for the door. I threw the camera at Garett and raced after him. For a moment I considered whether I should break one of the rules of autograph etiquette and tap Shaq on the shoulder. Fuck it.

“Hey Shaq, do you have time for one more? I’d really appreciate it.” The coat was soft.

He turned to find the voice. I was like a Prius in the blind spot of an 18-wheeler. He found me.

“Sure. No problem,” he said.

A few pen strokes later, Shaq handed me back the mini ball. I asked if he had just one more second for a picture.

“No problem,” he said.

It was at that second when a striking young woman—tall, thin and caramel-skinned—passed through the narrow space between us heading toward the elevator bank behind me. Time stopped. I looked up at Shaq.

“Hey, you can check her out while we take the picture,” I said.

I sidled up to Shaq, my head at his shoulder. I could feel the fur on my left ear as his huge paw enveloped my shoulder. I smiled huge and blinked away the flash before thanking Shaq and heading back toward my friends. I looked down at the ball. A few jagged blue lines resembled S—q 32. Score. Little did I know I’d soon follow it up with an assist of my own.

“Yo,” Shaq said. “Go get that girl’s number for me.”

His command spun me around. I was in shock. Down the hall the hot chick sat on a chair, legs folded, cell phone to her ear. Turning back to the giant, all I could do was laugh. Shaq’s eyebrows jumped, his head cocked back like a cat hearing the aluminum lid slide back on a tuna can.

Go get that girl’s number for me.”

He wasn’t kidding. I walked over to Garett and handed him my ball. I kept the pen. Flipping open my wallet, I searched frantically for a business card or receipt. Something I could write on.

“Shaq wants me to get that girl’s number for him,” I said pulling out a dirty, corner-dinged business card which I shoved in my pocket.

“That girl by the window?” Lewando said, looking past me. “Ha, good luck dude. Wait, isn’t Shaq married?”

As I took my first steps toward her, I had no idea what I was going to say but I knew I had to say something. I couldn’t remember when I last asked a girl for her number. At the time I had been with my girlfriend (who is now Mrs. Raymond) for over six years, meeting the first day of sophomore year of college. Needless to say, my game was a little rusty.

I stood a few strong steps away, far enough for her not to feel my stare. I looked left toward Shaq who gave me a nod. My mind raced. What do I say? It’s not like I could offer to buy her a drink. Isn’t there usually some sort of conversation that leads up to this? Did Shaq really think I had a better shot at getting a chick’s number than an NBA superstar worth a hundred million dollars? Seven hesitant steps and I was there. She was there.

The first thing I noticed was that she is not a hot chick at all. This young woman was astonishing. A light green scarf embellished in gold was wrapped tightly around her perfect head. Her long eyelashes flickered over watery blue eyes, a beautiful oddity given her complexion. Looking out the window at the traffic she held a small black flip phone in a French-manicured hand, only listening, as if to a girlfriend that just needed to vent. Her long skinny jeans looked painted on. I hovered until she looked up. The phone snapped shut and I flinched. She was totally outta my fucking league.

“Hi. I’m Matt.” I reached my hand out and it hung there forever before she took it. A Mona Lisa smile came across her face. I cast a look down the hall. “I was wondering if I could get your number for my boy over there?”

She turned right and her eyes rolled up at Shaq who was already towering over us. That was fast.

“Are you French?” he said in an expressionless baritone.

She smiled, with teeth this time. “Yes,” she said. There was hesitancy in the way she delivered this one word that indicated either her skepticism of where this was going or that she was still learning English. Maybe both. I was impressed by the accuracy of Shaq’s opener, even though he was undoubtedly a globetrotter. Still standing between him and the girl, I looked skyward for a follow-up.

“Are you a model?” he deadpanned.

I looked down at the girl. It was like I was watching a tennis match. Ping … pong.

Another smile, another yes. Although he was two for two, I started to question Shaq’s game. Seemed kind of weak for one of the most charismatic celebrities in the world. I also questioned why I am still standing here. Was I cramping Shaq’s style? I definitely was. Fuck it. I needed to see how this turned out.

Shaq reached a huge paw toward her, the same one that engulfed me a few minutes earlier. “Hi, I’m Tony Parker. I’m French too.”

I fought off a laugh at the thought of the real Parker, the San Antonio Spurs’ skinny point guard from France best known— at the time—as Mr. Eva Longoria. The young woman’s hand (and forearm) disappeared in Shaq’s grip but then she pulled back suddenly. She tilted her head and her eyes narrowed. “You’re not Tony Parker.”

“Yes, I am.”

She wagged a long fingernail at him. “I don’t know Tony Parker but I know you’re not him. I think he is more light-skinned than you.”

I thought it was funny that, in her mind, skin tone was what gave Shaq’s lie away—not the fact that the real Tony Parker was my size. The desire to hear his response was outweighed only by how uncomfortable I felt standing there—I’ve had too many positive interactions with celebrities (and girls, for that matter) end poorly by hanging around too long. But before this third wheel rolled away, I gave Shaq a nod of approval and a pat on the arm.

My job here was done.

This story does not appear in Shaq’s memoir, Shaq Uncut: My Story.

About the author: is the founder of Autograph University. He lives in the Boston area with his wife and two sons. Connect with him on Twitter at @mattraymond.

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